Sugiyama Toru, Hasegawa Genki, Niikura Chie, Kuwata Keiko, Imamura Yasutada, Demizu Yosuke, Kurihara Masaaki, Kittaka Atsushi
Faculty of Pharmaceutical Sciences, Teikyo University, Itabashi-ku, Tokyo 173-8605, Japan.
Faculty of Pharmaceutical Sciences, Teikyo University, Itabashi-ku, Tokyo 173-8605, Japan.
Bioorg Med Chem Lett. 2017 Aug 1;27(15):3337-3341. doi: 10.1016/j.bmcl.2017.06.015. Epub 2017 Jun 3.
Here we report the synthesis of new PNA monomers for pseudocomplementary PNA (pcPNA) that are fully compatible with standard Fmoc chemistry. The thiocarbonyl group of the 2-thiouracil (sU) monomer was protected with the 4-methoxy-2-methybenzyl group (MMPM), while the exocyclic amino groups of diaminopurine (D) were protected with Boc groups. The newly synthesized monomers were incorporated into a 10-mer PNA oligomer using standard Fmoc chemistry for solid-phase synthesis. Oligomerization proceeded smoothly and the HPLC and MALDI-TOF MS analyses indicated that there was no remaining MMPM on the sU nucleobase. The new PNA monomers reported here would facilitate a wide range of applications, such as antigene PNAs and DNA nanotechnologies.
在此，我们报道了用于假互补肽核酸（pcPNA）的新型肽核酸单体的合成，这些单体与标准芴甲氧羰基（Fmoc）化学完全兼容。2-硫代尿嘧啶（sU）单体的硫羰基用4-甲氧基-2-甲基苄基（MMPM）保护，而二氨基嘌呤（D）的环外氨基用叔丁氧羰基（Boc）保护。使用标准Fmoc化学固相合成法将新合成的单体掺入10聚体肽核酸低聚物中。低聚反应顺利进行，高效液相色谱（HPLC）和基质辅助激光解吸电离飞行时间质谱（MALDI-TOF MS）分析表明，sU核碱基上没有残留的MMPM。本文报道的新型肽核酸单体将促进广泛的应用，如反基因肽核酸和DNA纳米技术。
